ID: ALA1099205

Max Phase: Preclinical

Molecular Formula: C19H23NO4

Molecular Weight: 329.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1c1ccccc1

Standard InChI:  InChI=1S/C19H23NO4/c1-5-23-18(21)15-12(3)20-13(4)16(19(22)24-6-2)17(15)14-10-8-7-9-11-14/h7-11,17,20H,5-6H2,1-4H3

Standard InChI Key:  VQZSDRXKLXBRHJ-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 329.40

Molecular Weight (Monoisotopic): 329.1627

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.50

References

1. Fossheim R, Svarteng K, Mostad A, Rømming C, Shefter E, Triggle DJ..  (1982)  Crystal structures and pharmacological activity of calcium channel antagonists: 2,6-dimethyl-3,5-dicarbomethoxy-4-(unsubstituted, 2-methyl-, 4-methyl-, 3-nitro-, 4-nitro-, and 2,4-dinitrophenyl)-1,4-dihydropyridine.,  25  (2): [PMID:7057416] [10.1021/jm00344a007]

2. Böcker RH, Guengerich FP..  (1986)  Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450.,  29  (9): [PMID:3746811] [10.1021/jm00159a007]

3. Chang CC, Cao S, Kang S, Kai L, Tian X, Pandey P, Dunne SF, Luan CH, Surmeier DJ, Silverman RB..  (2010)  Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels Ca V 1.3 and Ca V 1.2.,  18  (9): [PMID:20382537] [10.1016/j.bmc.2010.03.038]

4. Waghmare A, Kanyalkar M, Joshi M, Srivastava S..  (2011)  In-vitro metabolic inhibition and antifertility effect facilitated by membrane alteration: search for novel antifertility agent using nifedipine analogues.,  46  (9): [PMID:21632156] [10.1016/j.ejmech.2011.05.022]

5. Visentin S, Ermondi G, Medana C, Pedemonte N, Galietta L, Caron G..  (2012)  Ligand-based design, in silico ADME-Tox filtering, synthesis and biological evaluation to discover new soluble 1,4-DHP-based CFTR activators.,  55  [PMID:22889557] [10.1016/j.ejmech.2012.07.017]

6. Murthy YL, Rajack A, Taraka Ramji M, Jeson babu J, Praveen Ch, Aruna Lakshmi K..  (2012)  Design, solvent free synthesis, and antimicrobial evaluation of 1,4 dihydropyridines.,  22  (18): [PMID:22901391] [10.1016/j.bmcl.2012.05.003]

7. Amgoth SN, Porika M, Abbagani S, Garlapati A, Vanga MR.  (2013)  Synthesis, anticancer and MRP1 inhibitory activities of 4-alkyl/aryl-3,5-bis(carboethoxy/carbomethoxy)-1,4-dihydro-2,6-dimethylpyridines,  22  (1): [10.1007/s00044-012-9994-0]

8. Niaz H, Kashtoh H, Khan JA, Khan A, Wahab AT, Alam MT, Khan KM, Perveen S, Choudhary MI..  (2015)  Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase.,  95  [PMID:25817770] [10.1016/j.ejmech.2015.03.018]

Source

Source(1):

• Scientific Literature